cas 623-17-6, Furfuryl acetate | Articles data

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Preparation method of alkyl carboxylic acid furfuryl ester
The invention discloses a preparation method of alkyl carboxylic acid furfuryl ester and relates to furfuryl alcohol. The catalyst, the acylating agent, the acid binding agent and the solvent are uniformly mixed to obtain the alkyl carboxylic acid furfuryl ester compound. The method is high in selectivity, few in byproducts and mild in reaction condition, and has a certain industrial application prospect.
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Paragraph 0028; 0037-0038

(2021/11/27)

Preparation method of furfuryl alcohol ester
The invention discloses a preparation method of furfuryl alcohol ester. The preparation method comprises the following step: subjecting furfural, a bifunctional catalyst, an acylation reagent and a solvent to reacting under hydrogen pressure to obtain furfuryl alcohol ester. The method provided by the invention has the advantages of high selectivity, few byproducts, mild reaction conditions and certain industrial application prospect.
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Paragraph 0028-0029; 0036-0037

(2021/02/10)

Conversion of furfural to 2-methylfuran over CuNi catalysts supported on biobased carbon foams
In this study, carbon foams prepared from the by-products of the Finnish forest industry, such as tannic acid and pine bark extracts, were examined as supports for 5/5% Cu/Ni catalysts in the hydrotreatment of furfural to 2-methylfuran (MF). Experiments were conducted in a batch reactor at 503 K and 40 bar H2. Prior to metal impregnation, the carbon foam from tannic acid was activated with steam (S1), and the carbon foam from pine bark extracts was activated with ZnCl2 (S2) and washed with acids (HNO3 or H2SO4). For comparison, a spruce-based activated carbon (AC) catalyst and two commercial AC catalysts as references were investigated. Compressive strength of the foam S2 was 30 times greater than that of S1. The highest MF selectivity of the foam-supported catalysts was 48 % (S2, washed with HNO3) at a conversion of 91 %. According to the results, carbon foams prepared from pine bark extracts can be applied as catalyst supports.
Varila, Toni,M?kel?, Eveliina,Kupila, Riikka,Romar, Henrik,Hu, Tao,Karinen, Reetta,Puurunen, Riikka L.,Lassi, Ulla
p. 16 - 27
(2020/12/28)

ZWITTERIONIC CATALYSTS FOR (TRANS)ESTERIFICATION: APPLICATION IN FLUOROINDOLE-DERIVATIVES AND BIODIESEL SYNTHESIS
An amide/iminium zwitterion catalyst has a catalyst pocket size that promotes transesterification and dehydrative esterification. The amide/iminium zwitterions are easily prepared by reacting aziridines with aminopyridines. The reaction can be applied a wide variety of esterification processes including the large-scale synthesis of biodiesel. The amide/iminium zwitterions allow the avoidance of strongly basic or acidic condition and avoidance of metal contamination in the products. Reactions are carried out at ambient or only modestly elevated temperatures. The amide/iminium zwitterion catalyst is easily recycled and reactions proceed in high to quantitative yields.
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Paragraph 0013; 0028

(2021/01/29)

KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot
A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is
Gurawa, Aakanksha,Kumar, Manoj,Rao, Dodla S.,Kashyap, Sudhir
supporting information
p. 16702 - 16707
(2020/10/27)

Preparation method of alkyl furfuryl alcohol ester
The invention discloses a preparation method of alkyl furfuryl alcohol ester, which comprises the following step of reacting furfuryl alcohol, an esterification catalyst, an acylation reagent, an acid-binding agent and a solvent to obtain the alkyl furfuryl alcohol ester. The method provided by the invention has the advantages of high selectivity, few byproducts, mild reaction conditions and certain industrial application prospect.
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Paragraph 0030-0038; 0046-0059

(2020/12/31)

Proton-exchanged montmorillonite-mediated reactions of hetero-benzyl acetates: Application to the synthesis of Zafirlukast
Proton-exchanged montmorillonite (H-mont) with outstanding surface characteristics can provide abundant acidic sites in the mesopores, and serve as an efficient heterogeneous catalyst for the synthesis of heterocycle-containing diarylmethanes via Friedel-Crafts-like alkylation of (hetero)arenes by heterobenzyl acetates under mild reaction conditions without requiring any additives or an inert atmosphere. Using this strategy, the gram-scale synthesis of indole-containing diarylmethane 13 has been accomplished in good yield for the preparation of Zafirlukast. In addition, H-mont can be applied to the nucleophilic substitution reactions of heterobenzyl acetate 5p with a variety of alcohols and 1,3-dicarbonyl compounds.
Yang, Lei,Chen, Xuan,Ni, Kaidong,Li, Yuansheng,Wu, Jianhong,Chen, Weilin,Ji, Yin,Feng, Lili,Li, Fei,Chen, Dongyin
supporting information

(2020/06/28)

HMF and furfural: Promising platform molecules in rhodium-catalyzed carbonylation reactions for the synthesis of furfuryl esters and tertiary amides
A biomass involved rhodium-catalyzed carbonylative synthesis of furfuryl esters and tertiary amides has been developed. 5-Hydroxymethylfurfural (HMF) was used as both substrate and CO surrogate for the first time in a carbonylation reaction, and both alkyl and aryl iodides were tolerated well to afford the desired furfuryl esters in moderate to good yields. In addition, furfural was also utilized as a CO source for the synthesis of tertiary amides. A variety of tertiary amides were obtained in moderate to excellent yields with good functional groups compatibility. Notably, tertiary amines were used as the amine source through a C[sbnd]N bond cleavage pathway in the absence of additional oxidant.
Qi, Xinxin,Zhou, Rong,Ai, Han-Jun,Wu, Xiao-Feng
p. 215 - 221
(2019/11/25)

Manganese-mediated acetylation of alcohols, phenols, thiols, and amines utilizing acetic anhydride
Manganese(II) chloride-catalyzed acetylation of alcohols, phenols thiols and amines with acetic anhydride is reported. This method is environment-friendly and economically viable as it involves inexpensive, relatively benign catalyst, mild reaction condition, and simple workup. Acetylation is performed under the solvent-free condition at ambient temperature and acetylated products obtained in good to excellent yields. Primary, secondary heterocyclic amines, and phenols with various functional groups are smoothly acetylated in good yields. This method exhibits exquisite chemoselectivity, the amino group is preferentially acetylated in the presence of a hydroxyl/thiol group.
Jain, Isha,Sharma, Ramandeep,Malik, Payal
supporting information
p. 2952 - 2960
(2019/09/13)

Coating of polydopamine on polyurethane open cell foams to design soft structured supports for molecular catalysts
Polydopamine-coated polyurethane open cell foams are used as structured supports for molecular catalysts through the covalent anchoring of alkoxysilyl arms by the catechol groups of the mussel-inspired layer. This strong bonding prevents their leaching. No alteration of the mechanical properties of the flexible support is observed after repeated uses of the catalytic materials.
Ait Khouya, Ahmed,Mendez Martinez, Miguel L.,Bertani, Philippe,Romero, Thierry,Favier, Damien,Roland, Thierry,Guidal, Valentin,Bellière-Baca, Virginie,Edouard, David,Jierry, Lo?c,Ritleng, Vincent
supporting information
p. 11960 - 11963
(2019/10/11)

Amide/Iminium Zwitterionic Catalysts for (Trans)esterification: Application in Biodiesel Synthesis
A class of zwitterionic organocatalysts based on an amide anion/iminium cation charge pair has been developed. The zwitterions are easily prepared by reacting aziridines with aminopyridines. They are catalytically applicable to transesterifications and dehydrative esterifications. Mechanistic studies reveal that the amide anion and iminium cation work synergistically in activating the reaction partners, with the iminium cationic moiety interacting with the carbonyl substrates through nonclassical hydrogen bonding. The reaction can be applied to large-scale synthesis of biodiesel under mild conditions.
Lam, Ying-Pong,Ng, Wing-Hin,Tan, Fei,Tse, Ying-Lung Steve,Wang, Xinyan,Yeung, Ying-Yeung
p. 8083 - 8092
(2019/08/26)

Method for synthesizing furacilin under catalysis of supported catalyst
The invention discloses a method for synthesizing furacilin under catalysis of a supported catalyst and belongs to the field of chemical synthesis. A 5-nitrofurfural intermediate is synthesized from furfuryl alcohol used as a raw material through steps of esterification, nitration, deprotection, oxidation and the like, and then, 5-nitrofurfural and semicarbazide are subjected to a condensation reaction under the catalytic action of the supported catalyst CuO/CNTs to produce furacilin. The method is simple to operate, the adopted catalyst has the characteristics of being non-toxic, easy to remove and renewable, and the product yield is high.
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Paragraph 0006; 0017; 0023; 0028

(2018/06/26)

Synthesis and characterization of MCM-41@XA@Ni(II) as versatile and heterogeneous catalyst for efficient oxidation of sulfides and acetylation of alcohols under solvent-free conditions
Herein, Ni(II) immobilized on modified mesoporous silica MCM-41 was designed and synthesized via a facile sequential strategy. The structure of the catalyst was characterized by X-ray diffraction. The thermal property of the as-synthesized materials was studied using thermogravimetric-differential thermal analysis. The average particles size and morphology of MCM-41@XA@Ni(II) were investigated using scanning electron microscopy and transmission electron microscopy. This nanostructure catalyst was effective for the selective oxidation of sulfides and acetylation of alcohols in solvent-free conditions. The easy recyclability of the catalyst and their complete chemoselectivity toward the sulfur group of substrates in the oxidation of sulfides are important “green” attributes of this catalyst.
Nazarzadeh, Somayeh,Ghorbani-Choghamarani, Arash,Tahanpesar, Elham
p. 649 - 659
(2018/01/28)

Reusable and efficient polyvinylpolypyrrolidone-supported triflic acid catalyst for acylation of alcohols, phenols, amines, and thiols under solvent-free conditions
Abstract: A triflic acid-functionalized polyvinylpolypyrrolidone was prepared and fully characterized by FT-IR, TGA, and SEM. This super acidic solid catalyst shows high catalytic activity for selective acylation of alcohols, phenols, amines, and thiols with anhydrides under solvent-free conditions at room temperature. In addition, this method features an easy to handle solid super acid catalyst and an operationally simple procedure, affording the desired acylated products in excellent yields. Graphical abstract: [Figure not available: see fulltext.].
Tajbakhsh, Mahgol,Tajbakhsh, Mahmoud,Khaksar, Samad,Gazvini, Helia Janatian,Heidary, Marzieh
p. 1117 - 1122
(2017/05/10)

TiCl4/Et3N-Mediated Condensation of Acetate and Formate Esters: Direct Access to β-Alkoxy- and β-Aryloxyacrylates
A methodology to build (E)-β-alkoxy- and (E)-β-aryloxyacrylate moieties from acetate and formate esters promoted by the TiCl4/Et3N system is presented. The reaction is compatible with a broad range of structural skeletons and elapses through an unusual condensation pathway. Taking into account the obtained results, we propose a plausible mechanism involving a bimetallic titanium intermediate for this type of transformation.
álvarez-Calero, José María,Jorge, Zacarías D.,Massanet, Guillermo M.
supporting information
p. 6344 - 6347
(2016/12/23)

An approach to heterodiarylmethanes via sp2-sp3 Suzuki-Miyaura cross-coupling
The synthesis of a range of structurally diverse diarylmethanes via the Suzuki-Miyaura cross-coupling of aryl methane acetates and arylboronic acids is reported, including several challenging examples containing nitrogen, oxygen and sulfur heteroatoms in one or both coupling partners. A single set of optimized conditions was used to generate the diarylmethanes in 52-91% yield.
Stewart, Gavin W.,Maligres, Peter E.,Baxter, Carl A.,Junker, Ellyn M.,Krska, Shane W.,Scott, Jeremy P.
p. 3701 - 3706
(2016/06/06)

Tetraethylammonium hydrogen carbonate: A cheap, efficient, and recyclable catalyst for transesterification reactions under solvent-free conditions
Tetraethylammonium hydrogen carbonate (TEAHC) was proven to be an efficient catalyst for transesterification reactions in the absence of solvent. The reaction between isopropenyl or ethyl acetate and an alcohol (not efficient in the absence of catalyst) was induced by the presence of TEAHC, which seems to assist the proton transfer from the alcohol to the ester, yielding the corresponding acetate in very good yields in the absence of any solvent. Moreover, the TEAHC can be recycled several times without significant loss in activity.
Chiarotto, Isabella
supporting information
p. 1840 - 1847
(2016/11/18)

Selective acetylation of primary alcohols by ethyl acetate
A KOtBu and ethyl acetate mediated efficient methodology has been developed for the acetylation of primary and secondary alcohols where ethyl acetate is the source of acetyl group. The reaction is fast, mild, efficient, and highly selective towards the primary alcohols.
Singha, Raju,Ray, Jayanta K.
p. 5395 - 5398
(2016/11/11)

Study of the diels-alder and retro-diels-alder reaction between furan derivatives and maleimide for the creation of new materials
The Diels-Alder reaction leads to a mixture of two diastereomers, one called endo and the other one exo. The cyclo-reversion temperature of the first one is lower than the exo adduct and the ratio between endo and exo adducts varies according to the substituents of the Diels-Alder partners and experimental parameters. Therefore, the influence of some reaction parameters such as the substituents of furan and maleimide derivatives, the reaction temperature and the presence of a nucleophile on the endo/exo Diels-Alder ratio and/or the retro-Diels-Alder reaction have been studied. For instance, furan and maleimide derivatives with electron withdrawing substituents induced the creation of the endo adduct preferentially. Also the presence of a far electron withdrawing substituent on furan and/or an electron attracting mesomeric substituent on maleimide resulted in a faster reversibility of the endo adduct. Finally, a high temperature and the presence of a nucleophile (thiol) also induced faster retro-Diels-Alder kinetics. Moreover, it was proved that isomerization from the endo to the exo diastereomer is preceded by a retro-Diels-Alder reaction of the endo adduct. The presence of a nucleophile in the mixture confirmed this result. This study allowed the highlighting of different parameters of the Diels-Alder reaction to obtain as much endo adduct as possible, and a fast and/or full retro-Diels-Alder reaction of this adduct.
Froidevaux,Borne,Laborbe,Auvergne,Gandini,Boutevin
p. 37742 - 37754
(2015/05/13)

Heterobimetallic dinuclear lanthanide alkoxide complexes as acid-base difunctional catalysts for transesterification
A practical lanthanide(III)-catalyzed transesterification of carboxylic esters, weakly reactive carbonates, and much less-reactive ethyl silicate with primary and secondary alcohols was developed. Heterobimetallic dinuclear lanthanide alkoxide complexes [Ln2Na8{(OCH2CH2NMe2)}12(OH)2] (Ln = Nd (I), Sm (II), and Yb (III)) were used as highly active catalysts for this reaction. The mild reaction conditions enabled the transesterification of various substrates to proceed in good to high yield. Efficient activation of transesterification may be endowed by the above complexes as cooperative acid-base difunctional catalysts, which is proposed to be responsible for the higher reactivity in comparison with simple acid/base catalysts.
Zeng, Ruijie,Sheng, Hongting,Zhang, Yongcang,Feng, Yan,Chen, Zhi,Wang, Junfeng,Chen, Man,Zhu, Manzhou,Guo, Qingxiang
p. 9246 - 9252
(2014/12/11)

Iron (III) phosphate as a green and reusable catalyst promoted chemo selective acetylation of alcohols and phenols with acetic anhydride under solvent free conditions at room temperature
Iron (III) phosphate was employed as an efficient catalyst for the chemo selective acetylation of alcohols and phenols under solvent free condition at room temperature and with high yields. Iron (III) phosphate is also a potential green catalyst due to solid intrinsically, reusable and with high catalytic activity.
Behbahani,Farahani,Oskooie
experimental part
p. 633 - 637
(2011/10/08)

Bifunctional Pd/Al-SBA-15 catalyzed one-step hydrogenation-esterification of furfural and acetic acid: A model reaction for catalytic upgrading of bio-oil
Al-SBA-15 supported palladium bifunctional catalysts were evaluated for one-step hydrogenation-esterification (OHE) of furfural and acetic acid as a model reaction for bio-oil upgrading. Experimental results show that it is viable to convert these unstable constituents of bio-oil to esters and alcohols through this simple and effective OHE reaction. The results of NH 3-TPD and catalytic performances show that Al-SBA-15 with medium ratio of Si/Al favors the OHE reaction between furfural and acetic acid. It is noteworthy that there is a synergistic effect between the metal sites and the acid sites over composite bifunctional catalyst of 5%Pd/Al-SBA-15 for the OHE reaction.
Yu, Wanjin,Tang, Yang,Mo, Liuye,Chen, Ping,Lou, Hui,Zheng, Xiaoming
scheme or table
p. 35 - 39
(2012/06/29)

Significant heterogeneous carbonate salt catalyzed acetylation of alcohols via a transesterification process with carbonate salt-activated alcohol 1H NMR evidence
Heterogeneous carbonate salt catalyzed acetylation of alcohols via a transesterification process has been developed. Various esters are furnished up to 97% yield. Established procedure is simple and air-tolerant with readily available reagents. Ethyl acetate and isobutyl acetate are used as not only acetylating agents, but also reaction solvents in transesterification. Aliphatic linear alcohols, allylic alcohols and benzyl alcohols show high reactivities in the presence of 1 or 5 mol% Cs2CO3 at 125°C. Cesium carbonate can be recycled by pumping liquid phase out of reactor after reaction. During four cycle runs for reaction of 2-phenylethanol and ethyl acetate, high yields of phenethyl acetate are provided (>60% yield). Based on experiments and 1H NMR investigation, bifunctional catalysis is proposed, alcohol activated by carbonate ion is confirmed, and higher activity of catalytic amount than stoichiometric cesium carbonate is interpreted. Copyright
Xiong, Yan,Zhang, Xueqiang
experimental part
p. 1143 - 1148
(2012/03/26)

Photoionization mass spectrometry: A useful method to evaluate the pyrolysis process of glycoside flavor precursor
The thermal decomposition behavior and the pyrolysis products of benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (BGLU) were studied with synchrotron vacuum ultraviolet (VUV) photoionization mass spectrometry at temperatures of 300, 500 and 700 °C at 0.062 Pa. Several pyrolysis products and intermediates were identified by the measurement of photoionization mass spectra at different photon energies. The results indicated that the primary decomposition reaction was the cleavage of O-glycosidic bond of the glycoside at low temperature, proven by the discoveries of benzyloxy radical (m/z = 107) and glycon radical (m/z = 331) in mass spectra. As pyrolysis temperature increased from 300 to 700 °C, two possible pyrolytic modes were observed. This work reported an application of synchrotron VUV photoionization mass spectrometry in the study of the thermal decomposition of glycoside flavor precursor, which was expected to help understand the thermal decomposition mechanism of this type of compound. The possibility of this glycoside to be used as a flavor precursor in high temperature process was evaluated.
Ding, Yu,Cai, Ji-Bao,Qi, Fei,Su, Qing-De
experimental part
p. 290 - 295
(2011/10/13)

N,N′-dibromo-N,N′-1,2-ethanediylbis(benzene sulfonamide) as an efficient catalyst for acetylation and formylation of alcohols under mild conditions
An efficient method for the acylation and formylation of alcohols and phenols by using an acylating/formylating agent (acetic anhydride and formic acid) in the presence of a catalytic amount of N,N′-dibromo-N,N′-1, 2-ethanediylbis(benzene sulfonamide) under mild and solvent-free conditions at room temperature in good to excellent yields is described. The use of protic acids and metal Lewis acids is avoided.
Khazaei, Ardeshir,Rostami, Amin,Rosta, Zahra,Alavi, Ali
experimental part
p. 181 - 186
(2010/04/05)

P-Toluenesulfonyl chloride as a new and effective catalyst for acetylation and formylation of hydroxyl compounds under mild conditions
The catalytic application of p-toluenesulfonyl chloride for efficient acetylation of various types of alcohols and phenols with acetic anhydride in solvent-free conditions is reported. Also structurally diverse alcohols were formylated using formic acid based on the use of catalytic amount of p-toluenesulfonyl chloride under solvent-free condition. The reactions were carried out in short reaction time and in good to excellent yields at room temperature.
Khazaei, Ardeshir,Rostami, Amin,Mantashlo, Fatemeh
experimental part
p. 1430 - 1434
(2011/10/08)

Synthesis and structure of an extremely air-stable binuclear hafnocene perfluorooctanesulfonate complex and its use in lewis acid-catalyzed reactions
An extremely air-stable μ2-hydroxy-bridged binuclear hafonocene perfluorooctanesulfoante complex was successfully synthesized. This complex showed high catalytic efficiency in the esterification of alcohols, phenol, thiol, and amines, in the Friedel-Crafts acylation of alylaryl ethers, in the Mukaiyama aldol reaction, and in the allylation of aldehydes and could be reused.
Qiu, Renhua,Zhang, Guoping,Zhu, Yuyang,Xu, Xinhua,Shao, Lingling,Li, Yinhui,An, Delie,Yin, Shuangfeng
supporting information; scheme or table
p. 6488 - 6494
(2010/02/28)

Trimethylsilylation of alcohols and phenols, and direct acetylation of silyl ethers catalyzed by Fe(ClO4)3.6H2O
In this article, a mild and efficient protocol for the trimethylsilylation of various aliphatic and benzylic alcohols and phenols with trimethylsilyl chloride using a catalytic amount of ferric perchlorate at room temperature and relatively short reaction times in good to excellent yields is reported. Direct acetylation of trimethylsilyl ethers catalyzed with Fe(ClO4)3.6H2O(0.02 mmol)/Fe(ClO4)3SiO2(0.2 g) using acetic anhydride at ambient temperature is also reported.
Oskooie, Hossein A.,Heravi, Majid M.,Tehrani, Maryam H.,Behbahani, Farahnaz K.,Heravi, Omid M.
experimental part
p. 1729 - 1737
(2010/01/17)

Polymer-supported gadolinium triflate as a convenient and efficient Lewis acid catalyst for acetylation of alcohols and phenols
A polymer-supported gadolinium triflate (CMPS-IM-Gd) catalyst was prepared from chloromethyl polystyrene (CMPS) resin using a simple and convenient procedure. This polymeric catalyst was used as an efficient Lewis acid catalyst for the acetylation of various alcohols and phenols with acetic anhydride, affording high yields under mild conditions. The reaction was completed in a short period of time with small amounts of the catalyst. The catalyst was reused over 10 times without any significant loss of its catalytic activity.
Yoon, Hyo-Jin,Lee, Sang-Myung,Kim, Jong-Ho,Cho, Hong-Jun,Choi, Jung-Woo,Lee, Sang-Hyeup,Lee, Yoon-Sik
p. 3165 - 3171
(2008/09/20)

SbCl3 as a highly efficient catalyst for the acetylation of alcohols, phenols, and amines under solvent-free conditions
Antimony trichloride has been found to be an efficient and expedient catalyst for the acylation of alcohols, phenols, amines, and sugars with acetic anhydride in high yields and in a short reaction time under solvent-free conditions at room temperature. Also, racemization of chiral alcohols and epimerization of sugars were not observed in any of the substrates. Copyright Taylor & Francis Group, LLC.
Bhattacharya, Asish K.,Diallo, Mamadou A.,Ganesh, Krishna N.
p. 1518 - 1526
(2008/09/20)

Ruthenium(III) acetylacetonate [Ru(acac)3] -An efficient recyclable catalyst for the acetylation of phenols, alcohols, and amines under neat conditions
A catalytic amount of ruthenium(III) acetylacetonate (2 mol%) [Ru(acac)3] enables solvent-free acetylation of phenols, alcohols, and amines at ambient temperature in good to excellent yields. Furthermore, the catalyst could be recovered and reused at least three times without a significant loss in yields.
Varala, Ravi,Nasreen, Aayesha,Adapa, Srinivas R.
p. 148 - 152
(2008/02/11)

A highly selective, high-speed, and hydrolysis-free O-acylation in subcritical water in the absence of a catalyst
(Chemical Equation Presented) Fast and furious: A wide range of alcohols are acylated by acetic anhydride, in the absence of catalyst, in subcritical water in a flow-type microreaction system. The esters are selectively produced in high yields at temperatures of 200 to 250°C. Varying the amount of acetic anhydride added with respect to the alcohols allows the regioselective acylation of one or both hydroxy groups of various dihydroxy compounds (see picture).
Sato, Masahiro,Matsushima, Keiichiro,Kawanami, Hajime,Ikuhsima, Yutaka
p. 6284 - 6288
(2008/04/05)

Selective acetylation of alcohols and amines with ethyl acetate in the presence of H6[PMo9V3O40] as the catalyst
Acetylation of various alcohols and benzyl amine was tested in the presence of H6[PMo9V3O40], a mixed addenda heteropolyacid, in ethyl acetate under reflux condition. Phenols and anilines are not affected under the reaction conditions. Selective transestrification of alcohols can be achieved in the presence of phenol and aniline derivatives using this method. Springer-Verlag 2007.
Heravi, Majid M.,Bakhtiari, Khadijeh,Javadi, Negar M.,Oskooie, Hossein A.,Bamoharram, Fatemeh F.
p. 445 - 447
(2008/02/02)

A novel 3-nitrobenzeneboronic acid as an extremely mild and environmentally benign catalyst for the acetylation of alcohols under solvent-free conditions
A novel 3-nitrobenzeneboronic acid is found to catalyse efficiently the acetylation of a wide range of alcohols as well as phenols with acetic anhydride in good to excellent yields at room temperature under solvent-free conditions. The reactions are clean and the catalyst is mild such that highly sensitive functional groups including oximes are stable to the reaction conditions.
Tale,Adude
p. 7263 - 7265
(2007/10/03)

Fluorous distannoxane-catalyzed acetylation of alcohols in heterogeneous single fluorous solvent system
Acetylation of alcohols with an equivalent amount of acetic anhydride is feasible in the presence of fluorous distannoxane catalyst in heterogeneous single fluorous system. The fluorous layer containing catalyst can be recycled and reused at least 10 times.
Peng, Zhihong,Orita, Akihiro,An, Delie,Otera, Junzo
p. 3187 - 3189
(2007/10/03)

P2O5 / SiO2 as a mild and efficient reagent for acylation of alcohols, phenols and amines under solvent-free conditions
P2O5 / SiO2 is a highly efficient reagent for the acetylations of a variety of alcohols, phenols and amines with acetic anhydride under solvent-free conditions. Primary, secondary, allylic and benzylic alcohols, diols and phenols with electron-donating or withdrawing substituents can be easily acetylated in good to excellent yield.
Eshghi, Hossein,Shafieyoon, Parvaneh
p. 802 - 805
(2007/10/03)

Structure-based design of a highly selective catalytic site-directed inhibitor of Ser/Thr protein phosphatase 2B (calcineurin)
Protein serine/threonine phosphatases (PP1, PP2A and PP2B) play important roles in intracellular signal transductions. The immunosuppressant drugs FK506 and cyclosporin A (CsA) bind to immunophilins, and these complexes selectively inhibit PP2B (calcineurin), leading to the suppression of T-cell proliferation. Both FK506 and CsA must, however, form complexes with immunophilins to exert their inhibitory action on PP2B. Thus, it is of interest to find a direct and selective inhibitor of PP2B that does not involve the immunophilins as a biological tool for studies of PP2B and also as a candidate therapeutic agent. We selected the simple natural product cantharidin, a known PP2A-selective inhibitor, as a lead compound for this project. Primary SAR indicated that norcantharidin (7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride) inhibits not only PP1 and PP2A but also PP2B, and a binding model of norcantharidin carboxylate to the PP2B catalytic site was computationally constructed. Based on this binding model, we designed and synthesized several cantharidin derivatives. Among these compounds, 1,5-dibenzoyloxymethyl-substituted norcantharidin was found to inhibit PP2B without inhibiting PP1 or PP2A. To our knowledge, this is the first highly selective catalytic site-directed inhibitor of PP2B.
Baba, Yoshiyasu,Hirukawa, Nozomu,Tanohira, Naoto,Sodeoka, Mikiko
p. 9740 - 9749
(2007/10/03)

Rapid and efficient acetylation of alcohols and phenols with acetic anhydride using tin(IV) porphyrin as catalyst
The efficient and rapid esterification of alcohols and phenols in acetic anhydride was achieved by tin(IV) tetraphenylporphyrin perchlorate [SnIV (tpp) (ClO4)2] as catalyst in high yields. SnIV (tpp) (ClO4)2 showed highly catalytic activity on the acetylation reaction.
Tangestaninejad, Shahram,Habibi, Mohammad Hossein,Mirkhani, Valiollah,Moghadam, Majid
p. 1337 - 1343
(2007/10/03)

Lithium perchlorate catalyzed acetylation of alcohols under mild reaction conditions
Lithium perchlorate is found to efficiently catalyze the acetylation of alcohols and phenols with acetic anhydride in good to excellent yields.
Nakae,Kusaki,Sato
p. 1584 - 1586
(2007/10/03)

Highly powerful and practical acylation of alcohols with acid anhydride catalyzed by Bi(OTf)3
Bi(OTf)3-catalyzed acylation of alcohols with acid anhydride was evaluated in comparison with other acylation methods. The Bi(OTf)3/acid anhydride protocol was so powerful that sterically demanding or tertiary alcohols could be acylated smoothly. Less reactive acylation reagents such as benzoic and pivalic anhydride are also activated by this catalysis. In these cases, a new technology was developed in order to overcome difficulty in separation of the acylated product from the remaining acylating reagent: methanolysis of the unreacted anhydride into easily separable methyl ester realized quite easy separation of the desired acylation product. The Bi(OTf)3/acid anhydride protocol was applicable to a wide spectrum of alcohols bearing various functionalities. Acid-labile THP- or TBS-protected alcohol, furfuryl alcohol, and geraniol could be acylated as well as base-labile alcohols. Even acylation of functionalized tertiary alcohols was effected at room temperature.
Orita,Tanahashi,Kakuda,Otera
p. 8926 - 8934
(2007/10/03)

Highly selective one-pot conversion of THP and MOM ethers to acetates by indium triiodide-catalysed deprotection and subsequent transesterification by ethyl acetate
The chemoselective one-pot conversion of tetrahydropyranyl (THP) and methoxymethyl (MOM) ethers of primary alcohols to the corresponding acetates was presented. It was done using indium triiodide-catalysed deprotection and subsequent acetylation by ethyl acetate through a transesterification process. The advantages offered by the method included operational simplicity, 'green' methodology involving no toxic or hazardous chemicals and high yield.
Ranu, Brindaban C.,Hajra, Alakananda
p. 2262 - 2265
(2007/10/03)

Highly efficient and versatile acylation of alcohols with Bi(OTf)3 as catalyst
A very convenient route for the acylation of alcohols is provide by using a Bi(OTf)3 catalyst [Eq. (1)]. In this protocol hindered and functionalized alcohols are acylated at 25°C, and solvents can be employed without purification. R= primary, secondary, tertiary alkyl, aryl; R'=Me, Ph, tBu.
Orita, Akihiro,Tanahashi, Chiaki,Kakuda, Atsushi,Otera, Junzo
p. 2877 - 2879
(2007/10/03)

Rapid preparation of variously protected glycals using titanium(III)
Glycosyl chlorides and bromides can be rapidly converted to glycals in high yield by reaction with (Cp2Ti[III]Cl)2. This reagent tolerates a wide range of common carbohydrate protecting groups, including silyl ethers, acetals, and esters; the methodology provides a general route for the preparation of glycals substituted with both acid- and base-labile functionality. A reaction mechanism is proposed that is based on heteroatom abstraction to give an intermediate glycosyl radical. This radical reacts with a second equivalent of Ti(III) to yield a glycosyltitanium(IV) species. β-Heteroatom elimination from the glycosyltitanium(IV) complex gives the glycal.
Spencer, Roxanne P.,Cavallaro, Cullen L.,Schwartz, Jeffrey
p. 3987 - 3995
(2007/10/03)

Mild and practical acylation of alcohols with esters or acetic anhydride under distannoxane catalysis
Distannoxane catalysts effect acylation of alcohols by action of esters and acetic anhydride. In particular, use of enol esters provides an extremely useful method. Primary alcohols are acylated in preference to secondary ones as well as phenol. Both acid- and base-sensitive functional groups remain intact. Especially unique is the discrimination of thio function which is completely tolerant under the present reaction conditions. This method is highly practical since operation is quite simple. Esters and solvents can be used without purification and no inert atmosphere is necessary. The products can be isolated simply by column chromatography or distillation without aqueous workup.
Orita, Akihiro,Sakamoto, Katsumasa,Hamada, Yuji,Mitsutome, Akihiro,Otera, Junzo
p. 2899 - 2910
(2007/10/03)

Synthesis of C-disaccharides via glucal dimerisation
Treatment of 3-O-acetyl glucal and related species with acetylperchlorate provides good yields of the corresponding C-disaccharides with a high degree of stereocontrol at the new C-C bond. Copyright (C) 1996 Elsevier Science Ltd.
Byerley, Andrew L. J.,Kenwright, Alan M.,Steel, Patrick G.
p. 9093 - 9096
(2007/10/03)

Esterification of furfuryl alcohol and its derivates
Furfuryl alcohol is esterified by means of an aliphatic anhydride or its halogen derivative using aliphatic, tertiary amines as catalysts.
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(2008/06/13)